Isopentyl carboxanilides for combating undesired micro-organisms

ABSTRACT

This invention relates to novel isopentylcarboxanilides of the formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in which L, R 1 , R 3  and A are as defined in the disclosure, to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP2004/011408, filed Oct. 12, 2004,which was published in German as International Patent Publication WO2005/042494 on May 12, 2005, and is entitled to the right of priority ofGerman Patent Applications 10349498.7, filed Oct. 23, 2003, and10352067.8, filed Nov. 7, 2003.

The present invention relates to novel isopentylcarboxanilides, to aplurality of processes for their preparation and to their use forcontrolling unwanted microorganisms.

It is already known that numerous carboxanilides have fungicideproperties (cf., for example, WO 02/059086, WO 00/09482, EP-A 0 824 099,EP-A 0 755 927, EP-A 0 589 301, EP-A 0 545 099, JP 11-335364, JP10-310577 and JP 10-251240). Known are, for example,1-methyl-N-[2-(3-methylbutyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide(from EP-A 0 824 099) and2,5-dimethyl-N-[3-(3-methylbutyl)phenyl]-3-furamide from (EP-A 0 755927). The activity of these compounds is good; however, it is sometimesunsatisfactory at low application rates.

This invention now provides novel isopentylcarboxanilides of the formula(I)

in which

-   L represents

-    where the bond labelled with * is attached to the amide, whereas    the bond labelled with # is attached to the alkyl side chain,-   R¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;    C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13    fluorine, chlorine and/or bromine atoms;    -   C₁-C₈-alkyl)carbonyl, (C₁-C₈-alkoxy)carbonyl,        (C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl, (C₃-C₈-cycloalkyl)carbonyl;        (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-haloalkoxy)carbonyl,        (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,        (C₃-C₈-halocycloalkyl)carbonyl having in each case 1 to 9        fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R⁴,        —CONR⁵R⁶ or —CH₂NR⁷R⁸,-   R² represents hydrogen, fluorine, chlorine, methyl or    trifluoromethyl,-   R³ represents hydrogen, halogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl,-   R⁴ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl; C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms,-   R⁵ and R⁶ independently of one another each represent hydrogen,    C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;    C₁-C₈-haloalkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,-   R⁵ and R⁶ furthermore together with the nitrogen atom to which they    are attached form a saturated heterocycle having 5 to 8 ring atoms    which is optionally mono- or polysubstituted by identical or    different substituents from the group consisting of halogen and    C₁-C₄-alkyl, where the heterocycle may contain 1 or 2 further    non-adjacent heteroatoms from the group consisting of oxygen,    sulphur and NR⁹,-   R⁷ and R⁸ independently of one another represent hydrogen,    C₁-C₈-alkyl, C₃-C₈-cycloalkyl; C₁-C₈-haloalkyl, C₃-C₈-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,-   R⁷ and R⁸ furthermore together with the nitrogen atom to which they    are attached form a saturated heterocycle having 5 to 8 ring members    which is optionally mono- or polysubstituted by identical or    different substituents from the group consisting of halogen and    C₁-C₄-alkyl, where the heterocycle may contain 1 or 2 further    non-adjacent heteroatoms from the group consisting of oxygen,    sulphur and NR⁹,-   R⁹ represents hydrogen or C₁-C₆-alkyl,-   A represents the radical of the formula (A1)

in which

-   -   R¹⁰ represents hydrogen, hydroxyl, formyl, cyano, halogen,        nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,        C₃-C₆-Cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or        C₁-C₄-haloalkylthio having in each case 1 to 5 halogen atoms,        aminocarbonyl or aminocarbonyl —C₁-C₄-alkyl,    -   R¹¹ represents hydrogen, halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl or        C₁-C₄-haloalkylthio having in each case 1 to 5 halogen atoms,        and    -   R¹² represents hydrogen, C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl,        C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-haloalkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl        having in each case 1 to 5 halogen atoms, or represents phenyl,    -   with the proviso that R¹⁰ does not represent iodine if R¹¹        represents hydrogen and    -   with the proviso that R¹⁰ does not represent trifluoromethyl or        difluoromethyl if R³ and R¹¹ represent hydrogen and R¹²        represents methyl,        or

-   A represents the radical (A2)

in which

-   -   R¹³ and R¹⁴ independently of one another represent hydrogen,        halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen        atoms and    -   R¹⁵ represents halogen, cyano or C₁-C₄-alkyl, or C₁-C₄-haloalkyl        or C₁-C₄-haloalkoxy having in each case 1 to 5 halogen atoms,        or

-   A represents the radical of the formula (A3)

in which

-   -   R¹⁶ and R¹⁷ independently of one another represents hydrogen,        halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen        atoms and    -   R¹⁸ represents hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1        to 5 halogen atoms,        or

-   A represents the radical of the formula (A4)

in which

-   -   R¹⁹ represents hydrogen, halogen, hydroxyl, cyano, C₁-C₆-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or C₁-C₄-haloalkylthio having        in each case 1 to 5 halogen atoms,        or

-   A represents the radical of the formula (A5)

in which

-   -   R²⁰ represents halogen, hydroxyl, cyano, C₁-C₄-alkyl,        C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl,        C₁-C₄-haloalkylthio or C₁-C₄-haloalkoxy having in each case 1 to        5 halogen atoms and    -   R²¹ represents hydrogen, halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy        having in each case 1 to 5 halogen atoms, C₁-C₄-alkylsulphinyl        or C₁-C₄-alkylsulphonyl,        or

-   A represents the radical of the formula (A6)

or

-   A represents the radical of the formula (A7)

in which

-   -   R²² represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5        halogen atoms,        or

-   A represents the radical of the formula (A8)

in which

-   -   R²³ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5        halogen atoms,        or

-   A represents the radical of the formula (A9)

in which

-   -   R²⁴ and R²⁵ independently of one another represents hydrogen,        halogen, amino, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5        halogen atoms and    -   R²⁶ represents hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1        to 5 halogen atoms, with the proviso that R²⁴ and R²⁶ do not        simultaneously represent methyl if R²⁵ represents hydrogen,        or

-   A represents the radical of the formula (A10)

in which

-   -   R²⁷ and R²⁸ independently of one another represent hydrogen,        halogen, amino, nitro, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1        to 5 halogen atoms and    -   R²⁹ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1        to 5 halogen atoms,        or

-   A represents the radical of the formula (A11)

in which

-   -   R³⁰ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,        di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms and    -   R³¹ represents halogen, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy having in        each case 1 to 5 halogen atoms,    -   with the proviso that R³¹ does not represent trifluoromethyl,        difluoromethyl or methyl if R³ represents hydrogen and R³⁰        represents methyl,        or

-   A represents the radical of the formula (A12)

in which

-   -   R³² represents hydrogen, halogen, amino, C₁-C₄-alkylamino,        di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms and    -   R³³ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1        to 5 halogen atoms,        or

-   A represents the radical of the formula (A13)

in which

-   -   R³⁴ represents hydrogen or C₁-C₄-alkyl and    -   R³⁵ represents halogen or C₁-C₄-alkyl,        or

-   A represents the radical of the formula (A14)

in which

-   -   R³⁶ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms,        or

-   A represents the radical of the formula (A15)

in which

-   -   R³⁷ represents halogen, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkylthio or        C₁-C₄-haloalkoxy having in each case 1 to 5 halogen atoms,        or

-   A represents the radical of the formula (A16)

in which

-   -   R³⁸ represents hydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl        having 1 to 5 halogen atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl,        hydroxy-C₁-C₄-alkyl, C₁-C₄-alkylsulphonyl,        di(C₁-C₄-alkyl)aminosulphonyl, C₁-C₆-alkylcarbonyl or in each        case optionally substituted phenylsulphonyl or benzoyl,    -   R³⁹ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms,    -   R⁴⁰ represents hydrogen, halogen, cyano, C₁-C₄-alkyl or        C₁-C₄-haloalkyl having 1 to 5 halogen atoms,    -   R⁴¹ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl        having 1 to 5 halogen atoms,    -   with the proviso that R⁴⁰ does not represent trifluoromethyl,        or

-   A represents the radical of the formula (A17)

in which

-   -   R⁴² represents C₁-C₄-alkyl.

If appropriate, the compounds according to the invention can be presentas mixtures of various possible isomeric forms, in particular ofstereoisomers, such as, for example, E and Z, threo and erythro, andalso optical isomers, and, if appropriate, also of tautomers. What isclaimed are both the E and the Z isomers, and also the threo and erythroand the optical isomers, any mixtures of these isomers and the possibletautomeric forms.

Furthermore, it has been found that isopentylcarboxanilides of theformula (I) are obtained when

-   a) carboxylic acid derivatives of the formula (II)

-   -   in which    -   A is as defined above and    -   X¹ represents halogen or hydroxyl,    -   are reacted with an aniline derivative of the formula (III)

-   -   in which L, R¹ and R³ are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of a condensing agent, if appropriate in the        presence of an acid binder and if appropriate in the presence of        a diluent,        or

-   b) isopentylcarboxanilides of the formula (I-a)

-   -   in which    -   L, A and R³ are as defined above    -   are reacted with halides of the formula (IV)        R^(1-A)—X²  (IV)    -   in which    -   X² represents chlorine, bromine or iodine,    -   R^(1-A) represents C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl,        C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₃-C₈-cycloalkyl; C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio,        C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,        halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl having in        each case 1 to 9 fluorine, chlorine and/or bromine atoms;        formyl, formyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,        (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;        halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,        halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl in each case having 1 to        13 fluorine, chlorine and/or bromine atoms;        (C₁-C₈-alkyl)carbonyl, (C₁-C₈-alkoxy)carbonyl,        (C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl, (C₃-C₈-Cycloalkyl)carbonyl;        (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-haloalkoxy)carbonyl,        (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,        (C₃-C₈-halocycloalkyl)carbonyl having in each case 1 to 9        fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R⁴,        CONR⁵R⁶ or —CH₂NR⁷R⁸,        -   where R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined above,    -   in the presence of a base and in the presence of a diluent,        or

-   c) isopentone derivatives of the formula (V)

-   -   in which    -   R¹, R², R³ and A are as defined above,    -   are reacted with hydrazine (or hydrazine hydrate) in the        presence of a base and, if appropriate, in the presence of a        diluent,        or

-   d) isopentene derivatives of the formula (VI)

-   -   in which R¹, R², R³ and A are as defined above,    -   are hydrogenated, if appropriate in the presence of a diluent        and if appropriate in the presence of a catalyst,        or

-   e) isopentyne derivatives of the formula (VII)

-   -   in which R¹, R², R³ and A are as defined above,    -   are hydrogenated, if appropriate in the presence of a diluent        and if appropriate in the presence of a catalyst.

Finally, it has been found that the novel isopentylcarboxanilides of theformula (I) have very good microbicidal properties and can be used forcontrolling unwanted microorganisms both in crop protection and in theprotection of materials.

The formula (I) provides a general definition of theisopentylcarboxanilides according to the invention. Preferred radicaldefinitions of the formulae shown above and below are given below. Thesedefinitions apply both to the end products of the formula (I) andlikewise to all intermediates.

-   L preferably represents L-1 where R² may in each case have the    general, preferred, particularly preferred, very particularly    preferred or especially preferred meanings.-   L furthermore preferably represents L-2.-   L furthermore preferably represents L-3.-   L furthermore preferably represents L-4.-   L particularly preferably represents L-1, where R² may in each case    have the general, preferred, particularly preferred, very    particularly preferred or especially preferred meanings.-   L furthermore particularly preferably represents L-2.-   L very particularly preferably represents L-1 where R² in each case    have the general, preferred, particularly preferred, very    particularly preferred or especially particularly preferred    meanings.-   R¹ preferably represents hydrogen, C₁-C₆-alkyl,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13    fluorine, chlorine and/or bromine atoms;    -   (C₁-C₆-alkyl)carbonyl, (C₁-C₄-alkoxy)carbonyl,        (C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl, (C₃-C₆-cycloalkyl)carbonyl;        (C₁-C₄-haloalkyl)carbonyl, (C₁-C₄-haloalkoxy)carbonyl,        (halo-C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl,        (C₃-C₆-halocycloalkyl)carbonyl having in each case 1 to 9        fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R⁴,        —CONR⁵R⁶ or —CH₂NR⁷R⁸.-   R¹ particularly preferably represents hydrogen, methyl, ethyl, n- or    isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl,    methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-,    sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or    isopropylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl,    methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl,    cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl,    trifluoroethyl, difluoromethylthio, difluorochloromethylthio,    trifluoromethylthio, trifluoromethylsulphinyl,    trifluoromethylsulphonyl, trifluoromethoxymethyl; formyl, —CH₂—CHO,    —(CH₂)₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂,    —(CH₂)₂—CO—CH₃, —(CH₂)₂—CO—CH₂CH₃, —(CH₂)₂—CO—CH(CH₃)₂, —CH₂—CO₂CH₃,    —CH₂—CO₂CH₂CH₃, —CH₂—CO₂CH(CH₃)₂, —(CH₂)₂—CO₂CH₃, —(CH₂)₂—CO₂CH₂CH₃,    —(CH₂)₂—CO₂CH(CH₃)₂, —CH₂—CO—CF₃, —CH₂—CO—CCl₃, —CH₂—CO—CH₂CF₃,    —CH₂—CO—CH₂CCl₃, —(CH₂)₂—CO—CH₂CF₃, —(CH₂)₂—CO—CH₂CCl₃,    —CH₂—CO₂CH₂CF₃, —CH₂—CO₂CF₂CF₃, —CH₂—CO₂CH₂CCl₃, —CH₂—CO₂CCl₂CCl₃,    —(CH₂)₂—CO₂CH₂CF₃, —(CH₂)₂—CO₂CF₂CF₃, —(CH₂)₂—CO₂CH₂CCl₃,    —(CH₂)₂—CO₂CCl₂CCl₃;    -   methylcarbonyl, ethylcarbonyl, n-propylcarbonyl,        isopropylcarbonyl, tert-butylcarbonyl, methoxycarbonyl,        ethoxycarbonyl, tert-butoxycarbonyl, cyclopropylcarbonyl;        trifluoromethylcarbonyl, trifluoromethoxycarbonyl, or        —C(═O)C(═O)R⁵, —CONR⁶R⁷ or —CH₂NR⁸R⁹.-   R¹ very particularly preferably represents hydrogen, methyl,    methoxymethyl, formyl, —CH₂—CHO, —(CH₂)₂—CHO, —CH₂—CO—CH₃,    —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂, —C(═O)CHO, —C(═O)C(═O)CH₃,    —C(═O)C(═O)CH₂OCH₃, —C(═O)CO₂CH₃, —C(═O)CO₂CH₂CH₃.-   R² preferably represents hydrogen.-   R² furthermore preferably represents fluorine, where fluorine is    particularly preferably located in the 4-, 5- or 6-position, very    particularly preferably in the 4- or 6-position, especially in the    4-position, of the anilide radical [cf. formula (I) above].-   R² furthermore preferably represents chlorine, where chlorine is    particularly preferably located in the 5-position of the anilide    radical [cf. formula (I) above]. Chlorine is furthermore    particularly preferably located in the 4-position of the anilide    radical.-   R² furthermore preferably represents methyl, where methyl is    particularly preferably located in the 3-position of the anilide    radical [cf. formula (I) above].-   R² furthermore preferably represents trifluoromethyl, where    trifluoromethyl is particularly preferably located in the 4- or    5-position of the anilide radical [cf. formula (I) above].-   R³ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, C₁-C₆-alkyl, C₁-C₆-haloalkyl having 1 to 13 fluorine,    chlorine and/or bromine atoms.-   R³ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, methyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl or    C₁-C₄-haloalkyl having 1 to 9 fluorine, chlorine and/or bromine    atoms.-   R³ very particularly preferably represents hydrogen fluorine,    chlorine or methyl, ethyl or trifluoromethyl.-   R⁴ preferably represents hydrogen, C₁-C₆-alkyl, C₁-C₄-alkoxy,    C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,    C₁-C₄-haloalkoxy, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms.-   R⁴ particularly preferably represents hydrogen, methyl, ethyl, n- or    iso-propyl, tert-butyl, methoxy, ethoxy, n- or isopropoxy,    tert-butoxy, cyclopropyl; trifluoromethyl, trifluoromethoxy.-   R⁵ and R⁶ independently of one another preferably represent    hydrogen, C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-Cycloalkyl;    C₁-C₄-haloalkyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms.-   R⁵ and R⁶ furthermore together with the nitrogen atom to which they    are attached preferably represent a saturated heterocycle having 5    to 8 ring atoms which is optionally mono- to tetrasubstituted by    identical or different substituents from the group consisting of    halogen and C₁-C₄-alkyl, where the heterocycle may contain 1 or 2    further non-adjacent heteroatoms from the group consisting of    oxygen, sulphur and NR⁹.-   R⁵ and R⁶ independently of one another particularly preferably    represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-    or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,    ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl,    trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.-   R⁵ and R⁶ furthermore together with the nitrogen atom to which they    are attached particularly preferably represent a saturated    heterocycle from the group consisting of morpholine, thiomorpholine    and piperazine which is optionally mono- to tetrasubstituted by    identical or different substituents from the group consisting of    fluorine, chlorine, bromine and methyl, where the piperazine may be    substituted on the second nitrogen atom by R9.-   R⁷ and R⁸ independently of one another preferably represent    hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,    C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms.-   R⁷ and R⁸ furthermore together with the nitrogen atom to which they    are attached preferably represent a saturated heterocycle having 5    to 8 ring atoms which is optionally mono- to tetrasubstituted by    identical or different substituents from the group consisting of    halogen and C₁-C₄-alkyl, where the heterocycle may contain 1 or 2    further non-adjacent heteroatoms from the group consisting of    oxygen, sulphur and NR⁹.-   R⁷ and R⁸ independently of one another particularly preferably    represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-    or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,    ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl,    trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.-   R⁷ and R⁸ furthermore together with the nitrogen atom to which they    are attached particularly preferably represent a saturated    heterocycle from the group consisting of morpholine, thiomorpholine    and piperazine which is optionally mono- to tetrasubstituted by    identical or different substituents from the group consisting of    fluorine, chlorine, bromine and methyl, where the piperazine may be    substituted on the second nitrogen atom by R⁹.-   R⁹ preferably represents hydrogen or C₁-C₄-alkyl.-   R⁹ particularly preferably represents hydrogen, methyl, ethyl, n- or    isopropyl, n-, iso-, sec- or tert-butyl.-   A particularly represents one of the radicals    -   A1, A2, A3, A4) A5, A6, A9, A10, A11, A12, A13, A14, A15 or A16        given above.-   A particularly preferably represents one of the radicals    -   A1, A2, A4, A5, A6, A9, A11, A12, A13, A14, A15 or A16 given        above.-   A very particularly preferably represents the radical A1.-   A furthermore very particularly preferably represents the radical    A2.-   A furthermore very particularly preferably represents the radical    A4.-   A furthermore ver particularly preferably represents the radical A5.-   A furthermore very particularly preferably represents the radical    A6.-   A furthermore very particularly preferably represents the radical    A9.-   A furthermore very particularly preferably represents the radical    A11.-   A furthermore very particularly preferably represents the radical    A12.-   A furthermore very particularly preferably represents the radical    A13.-   A furthermore very particularly preferably represents the radical    A14.-   A furthermore very particularly preferably represents the radical    A16.-   R¹⁰ preferably represents hydrogen, hydroxyl, formyl, cyano,    fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl,    methoxy, ethoxy, methylthio, ethylthio, cyclopropyl,    C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy having in each case 1 to 5    fluorine, chlorine and/or bromine atoms, trifluoromethylthio,    difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or    aminocarbonylethyl,    -   with the proviso that R¹⁰ does not represent iodine if R¹¹        represents hydrogen and with the proviso that R¹⁰ does not        represent trifluoromethyl or difluoromethyl if R³ and R¹¹        represent hydrogen and R¹² represents methyl.-   R¹⁰ particularly preferably represents hydrogen, hydroxyl, formyl,    fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl,    methoxy, ethoxy, monofluoromethyl, monofluoroethyl, difluoromethyl,    trifluoromethyl, difluorochloromethyl, trichloromethyl,    dichloromethyl, pentafluoroethyl, cyclopropyl, methoxy, ethoxy,    trifluoromethoxy, difluoromethoxy, trichloromethoxy, methylthio,    ethylthio, trifluoromethylthio or difluoromethylthio, with the    proviso that R¹⁰ does not represent iodine if R¹¹ represents    hydrogen and with the proviso that R¹⁰ does not represent    trifluoromethyl or difluoromethyl if R³ and R¹¹ represent hydrogen    and R¹² represents methyl.-   R¹⁰ very particularly preferably represents hydrogen, hydroxyl,    formyl, fluorine, chlorine, bromine, iodine, methyl, ethyl,    isopropyl, methoxy, cyclopropyl, monofluoromethyl, monofluoroethyl,    difluoromethyl, dichloromethyl, trifluoromethyl,    difluorochloromethyl, trichloromethyl, —CHFCH₃ or difluoromethoxy,    -   with the proviso that R¹⁰ does not represent iodine if R¹¹        represents hydrogen and with the proviso that R¹⁰ does not        represent trifluoromethyl or difluoromethyl if R³ and R¹¹        represent hydrogen and R¹² represents methyl.-   R¹⁰ especially preferably represents hydrogen, hydroxyl, formyl,    chlorine, methyl, ethyl, methoxy, cyclopropyl, monofluoromethyl,    difluoromethyl, dichloromethyl, trifluoromethyl, —CHFCH₃ or    difluoromethoxy,    -   with the proviso that R¹⁰ does not represent trifluoromethyl or        difluoromethyl if R³ and R¹¹ represent hydrogen and R¹²        represents methyl.-   R¹¹ preferably represents hydrogen, chlorine, bromine, iodine,    methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio,    C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms,-   R¹¹ particularly preferably represents hydrogen, chlorine, bromine,    iodine, methyl or —CHFCH₃.-   R¹¹ very particularly preferably represents hydrogen, chlorine,    methyl or —CHFCH₃.-   R¹² preferably represents hydrogen, methyl, ethyl, n-propyl,    isopropyl, C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or    bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl,    cyclopentyl, cyclohexyl or phenyl.-   R¹² particularly preferably represents hydrogen, methyl, ethyl,    isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl,    hydroxyethyl or phenyl.-   R¹² very particularly preferably represents hydrogen, methyl,    trifluoromethyl or phenyl.-   R¹² especially preferably represents methyl.-   R¹³ and R¹⁴ independently of one another preferably represent    hydrogen, fluorine, chlorine, bromine, methyl, ethyl or    C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R¹³ and R¹⁴ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, difluorochloromethyl or    trichloromethyl.-   R¹³ and R¹⁴ independently of one another very particularly    preferably represent hydrogen, fluorine, chlorine, bromine, methyl,    ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.-   R¹³ and R¹⁴ especially preferably each represent hydrogen.-   R¹⁵ preferably represents fluorine, chlorine, bromine, iodine,    cyano, methyl, ethyl, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy having in    each case 1 to 5 fluorine, chlorine and/or bromine atoms.-   R¹⁵ particularly preferably represents fluorine, chlorine, bromine,    iodine, cyano, methyl, trifluoromethyl, trifluoromethoxy,    difluoromethoxy, difluorochloromethoxy or trichloromethoxy.-   R¹⁵ very particularly preferably represents fluorine, chlorine,    bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy.-   R¹⁵ especially preferably represents chlorine or methyl.-   R¹⁶ and R¹⁷ independently of one another preferably represent    hydrogen, fluorine, chlorine, bromine, methyl, ethyl or    C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R¹⁶ and R¹⁷ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, difluorochloromethyl or    trichloromethyl.-   R¹⁶ and R¹⁷ independently of one another very particularly    preferably represent hydrogen, fluorine, chlorine, bromine or    methyl.-   R¹⁶ and R¹⁷ especially preferably each represent hydrogen.-   R¹⁸ preferably represents hydrogen, methyl, ethyl or C₁-C₂-haloalkyl    having 1 to 5 fluorine, chlorine and/or bromine atoms.-   R¹⁸ particularly preferably represents hydrogen, methyl or    trifluoromethyl.-   R¹⁸ very particularly preferably represents methyl.-   R¹⁹ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, hydroxyl, cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl,    C₁-C₂-haloalkoxy or C₁-C₂-haloalkylthio having in each case 1 to 5    fluorine, chlorine and/or bromine atoms.-   R¹⁹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl,    isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, difluoromethyl,    trifluoromethyl, difluorochloromethyl, trichloromethyl,    trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,    trichloromethoxy, trifluoromethylthio, difluoromethylthio,    difluorochloromethylthio or trichloromethylthio.-   R¹⁹ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl    or trichloromethyl.-   R¹⁹ especially preferably represents iodine, methyl, difluoromethyl    or trifluoromethyl.-   R²⁰ preferably represents fluorine, chlorine, bromine, iodine,    hydroxyl, cyano, C₁-C₄-alkyl, methoxy, ethoxy, methylthio,    ethylthio, difluoromethylthio, trifluoromethylthio, C₁-C₂-haloalkyl    or C₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R²⁰ particularly preferably represents fluorine, chlorine, bromine,    iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl,    n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl,    difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy,    ethoxy, methylthio, ethylthio, difluoromethylthio,    trifluoromethylthio, trifluoromethoxy, difluoromethoxy,    difluorochloromethoxy or trichloromethoxy.-   R²⁰ very particularly preferably represents fluorine, chlorine,    bromine, iodine, methyl, trifluoromethyl, difluoromethyl or    trichloromethyl.-   R²¹ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, cyano, C₁-C₄-alkyl, methoxy, ethoxy, methylthio, ethylthio,    C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy having in each case 1 to 5    fluorine, chlorine and/or bromine atoms, C₁-C₂-alkylsulphinyl or    C₁-C₂-alkylsulphonyl.-   R²¹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, iso-butyl,    sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio,    ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,    trichloromethoxy, methylsulphinyl or methylsulphonyl.-   R²¹ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, iso-butyl,    sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,    trichloromethyl, methylsulphinyl or methylsulphonyl.-   R²¹ especially preferably represents hydrogen.-   R²² preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1    to 5 fluorine, chlorine and/or bromine atoms.-   R²² particularly preferably represents methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R²² very particularly preferably represents methyl, trifluoromethyl,    difluoromethyl or trichloromethyl.-   R²³ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1    to 5 fluorine, chlorine and/or bromine atoms.-   R²³ particularly preferably represents methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R²³ very particularly preferably represents methyl, trifluoromethyl,    difluoromethyl or trichloromethyl.-   R²⁴ and R²⁵ independently of one another preferably represent    hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or    C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R²⁴ and R²⁵ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R²⁴ and R²⁵ independently of one another very particularly    preferably represent hydrogen, fluorine, chlorine, bromine or    methyl.-   R²⁴ and R²⁵ especially preferably each represent hydrogen.-   R²⁶ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,    chlorine and/or bromine atoms.-   R²⁶ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl or trichloromethyl.-   R²⁶ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, methyl or trifluoromethyl.-   R²⁶ especially preferably represents methyl or trifluoromethyl.-   R²⁷ and R²⁸ independently of one another preferably represent    hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R²⁷ and R²⁸ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, nitro, methyl,    ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R²⁷ and R²⁸ independently of one another very particularly    preferably represent hydrogen, fluorine, chlorine, bromine, methyl,    trifluoromethyl, difluoromethyl or trichloromethyl.-   R²⁷ and R²⁸ especially preferably each represent hydrogen.-   R²⁹ preferably represents fluorine, chlorine, bromine, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R²⁹ particularly preferably represents fluorine, chlorine, bromine,    methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl    or trichloromethyl.-   R²⁹ very particularly preferably represents fluorine, chlorine,    bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.-   R²⁹ especially preferably represents methyl.-   R³⁰ preferably represents hydrogen, fluorine, chlorine, bromine,    amino, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³⁰ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R³⁰ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, amino, methylamino, dimethylamino, methyl,    trifluoromethyl, difluoromethyl or trichloromethyl.-   R³⁰ especially preferably represents amino, methylamino,    dimethylamino, methyl or trifluoromethyl.-   R³¹ preferably represents fluorine, chlorine, bromine, hydroxyl,    methyl, ethyl, methoxy, ethoxy, cyclopropyl, C₁-C₂-haloalkyl or    C₁-C₂-haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³¹ particularly preferably represents fluorine, chlorine, bromine,    hydroxyl, methyl, ethyl, methoxy, ethoxy, cyclopropyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R³¹ very particularly preferably represent fluorine, chlorine,    bromine, hydroxyl, methyl, methoxy, cyclopropyl, trifluoromethyl,    difluoromethyl or trichloromethyl.-   R³² preferably represents hydrogen, fluorine, chlorine, bromine,    amino, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³² particularly preferably represents hydrogen, fluorine, chlorine,    bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R³² very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, amino, methylamino, dimethylamino, methyl,    trifluoromethyl, difluoromethyl or trichloromethyl.-   R³² especially preferably represents amino, methylamino,    dimethylamino, methyl or trifluoromethyl.-   R³³ preferably represents fluorine, chlorine, bromine, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³³ particularly preferably represents fluorine, chlorine, bromine,    methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl    or trichloromethyl.-   R³³ very particularly preferably represents fluorine, chlorine,    bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.-   R³³ especially preferably represents methyl, trifluoromethyl or    difluoromethyl.-   R³⁴ preferably represents hydrogen, methyl or ethyl.-   R³⁴ particularly preferably represents methyl.-   R³⁵ preferably represents fluorine, chlorine, bromine, methyl or    ethyl.-   R³⁵ particularly preferably represents fluorine, chlorine or methyl.-   R³⁶ preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R³⁶ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, methyl or trifluoromethyl.-   R³⁷ preferably represents fluorine, chlorine, bromine, iodine,    hydroxyl, C₁-C₄-alkyl, methoxy, ethoxy, methylthio, ethylthio,    difluoromethylthio, trifluoromethylthio, C₁-C₂-haloalkyl or    C₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R³⁷ particularly preferably represents fluorine, chlorine, bromine,    iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,    sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, trichloromethyl.-   R³⁷ very particularly preferably represents fluorine, chlorine,    bromine, iodine, methyl, trifluoromethyl, difluoromethyl or    trichloromethyl.-   R³⁸ preferably represents hydrogen, methyl, ethyl, C₁-C₂-haloalkyl    having 1 to 5 fluorine, chlorine and/or bromine atoms,    C₁-C₂-alkoxy-C₁-C₂-alkyl, hydroxymethyl, hydroxyethyl,    methylsulphonyl or dimethylaminosulphonyl.-   R³⁸ particularly preferably represents hydrogen, methyl, ethyl,    trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or    hydroxyethyl.-   R³⁸ very particularly preferably represents methyl or methoxymethyl.-   R³⁹ preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl or C₁₋₂-haloalkyl having 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R³⁹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or    trichloromethyl.-   R³⁹ very particularly preferably represents hydrogen or methyl.-   R⁴⁰ preferably represents hydrogen, fluorine, chlorine, bromine,    cyano, methyl, ethyl, isopropyl or C₁-C₂-haloalkyl having 1 to 5    fluorine, chlorine and/or bromine atoms.-   R⁴⁰ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, cyano, methyl, ethyl, isopropyl, trifluoromethyl,    difluoromethyl, difluorochloromethyl or trichloromethyl.-   R⁴⁰ very particularly preferably represents hydrogen, fluorine,    methyl or trifluoromethyl.-   R⁴¹ preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R⁴¹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, methyl or trifluoromethyl.-   R⁴¹ very particularly preferably represents hydrogen or    trifluoromethyl.-   R⁴² preferably represents methyl, ethyl, n-propyl or isopropyl.-   R⁴² particularly preferably represents methyl or ethyl.

Emphasis is given to compounds of the formula (I) in which L representsL-1, where R² has the general meanings given above.

Emphasis is given to compounds of the formula (I) in which L representsL-1, where R² has the preferred meanings given above.

Emphasis is given to compounds of the formula (I) in which L representsL-1, where R² has the particularly preferred meanings given above.

Emphasis is given to compounds of the formula (I) in which L representsL-1, where R² has the very particularly preferred meanings given above.

Emphasis is given to compounds of the formula (I) in which L representsL-1, where R² has the especially preferred meanings given above.

Emphasis is given to compounds of the formula (I) in which L representsL-2.

Emphasis is given to compounds of the formula (I) in which R¹ representshydrogen.

Emphasis is given to compounds of the formula (I) in which R¹ representsformyl.

Emphasis is furthermore given to compounds of the formula (I) in whichR¹ represents —C(═O)C(═O)R⁴ where R⁴ is as defined above.

Emphasis is given to compounds of the formula (I) in which A representsA1.

Emphasis is given to compounds of the formula (I) in which R³ representshydrogen.

Emphasis is given to compounds of the formula (I) in which R³ representshalogen, preferably fluorine, chlorine, bromine or iodine, particularlypreferably fluorine, chlorine or bromine, very particularly preferablyfluorine or chlorine.

Emphasis is given to compounds of the formula (I) in which R³ representsC₁-C₈-alkyl, preferably C₁-C₆-alkyl, particularly preferably methyl,ethyl, n-, isopropyl, n-, iso-, sec- or tert-butyl, very particularlypreferably methyl or ethyl.

Emphasis is given to compounds of the formula (I) in which R³ representsC₁-C₈-haloalkyl, preferably C₁-C₆-haloalkyl having 1 to 13 fluorine,chlorine and/or bromine atoms, particularly preferably C₁-C₄-haloalkylhaving 1 to 9 fluorine, chlorine and/or bromine atoms, very particularlypreferably trifluoromethyl.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched, as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, wherein the case of polysubstitution the substituents can be identical ordifferent.

Halogen-substituted radicals, such as, for example, haloalkyl, are mono-or polyhalogenated. In the case of polyhalogenation, the halogen atomscan be identical or different. Here, halogen represents fluorine,chlorine, bromine and iodine, in particular fluorine, chlorine andbromine.

However, the general or preferred radical definitions or illustrationsgiven above can also be combined with one another as desired, i.e.between the respective ranges and preferred ranges. The definitionsapply both to the end products and, correspondingly, to the precursorsand intermediates.

The definitions mentioned can be combined with one another as desired.Moreover, individual definitions may not apply.

Preference, particular preference or very particular preference is givento the compounds of the formula (I) which carry the substituentsmentioned as being preferred, particularly preferred and veryparticularly preferred, respectively.

Description of the Processes According to the Invention for Preparingthe Isopentylcarboxanilides of the Formula (I) and the Intermediates

Process (a)

Using 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride and[2-(3-methylbutyl)phenyl]amine as starting materials, the process (a)according to the invention can be illustrated by the following formulascheme:

The formula (II) provides a general definition of the carboxylic acidderivatives required as starting materials for carrying out the process(a) according to the invention. In this formula (II), A preferably,particularly preferably and very particularly preferably has thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for A. X¹ preferably representschlorine, bromine or hydroxyl.

The carboxylic acid derivatives of the formula (II) are known and/or canbe prepared by known processes (cf. WO 93/11117, EP-A 0 545 099, EP-A 0589 301 and EP-A 0 589 313).

The formula (III) provides a general definition of the anilinederivatives furthermore required as starting materials for carrying outthe process (a) according to the invention. In this formula (III), L, R¹and R³ preferably, particularly preferably and very particularlypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferredand very particularly preferred, respectively, for these radicals.

Some of the aniline derivatives of the formula (III) in which Lrepresents L-1 are novel. Aniline derivatives of the formula (III) inwhich L represents L-1 can be prepared by

-   f) reacting cyanoanilines of the formula (VIII)

-   -   in which R¹ and R² are as defined above    -   in a first step with a Grignard reagent of the formula (IX)

-   -   in which    -   R³ is as defined above,    -   X³ represents chlorine, bromine or iodine,    -   if appropriate in the presence of a diluent, and reacting the        resulting alkanoneanilines of the formula (X)

-   -   in which R¹, R² and R³ are as defined above    -   in a second step with hydrazine (or hydrazine hydrate) in the        presence of a base (for example alkali metal or alkaline earth        metal hydroxides, such as sodium hydroxide or potassium        hydroxide) and, if appropriate, in the presence of a diluent.

The formula (VIII) provides a general definition of the cyanoanilinesrequired as starting materials for carrying out the process (f)according to the invention. In this formula (VIII), R¹ and R²preferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for these radicals.

The cyanoanilines of the formula (VIII) are known and/or can be preparedby known processes. Cyanoanilines of the formula (VIII) in which R¹ doesnot represent hydrogen can be obtained by reacting cyanoanilines of theformula (V-a)

-   in which R² is as defined above-   with halides of the formula (IV)    R^(1-A)—X²  (IV)-   in which R^(1-A) is as defined above-   in the presence of a base and in the presence of a diluent. (The    reaction conditions of the process (b) apply correspondingly.]

The formula (IX) provides a general definition of the Grignard reagentsfurthermore required as starting materials for carrying out the process(f) according to the invention. In this formula (IX), R³ preferably,particularly preferably and very particularly preferably has thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for this radical. X³ preferablyrepresents bromine.

The Grignard reagents of the formula (IX) are known or can be obtainedby known processes.

The alkanoneanilines of the formula (X), which are intermediates in theprocess (f) according to the invention, are novel and also form part ofthe subject-matter of this application. In the formula (X), the radicalsR¹, R² and R³ preferably, particularly preferably and very particularlypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferredand very particularly preferred, respectively, for these radicals.

Hydrazine (or hydrazine hydrate), which is also required as a reagentfor the process (f) according to the invention, is a known chemical forsynthesis.

The process (f) according to the invention can be carried out in variousvariants. Thus, it is possible to initially convert cyanoanilines of theformula (V-a) into the corresponding alkanoneanilines of the formula(VII-a)

-   in which R² and R³ are as defined above,-   which are then, if appropriate, reacted with halides of the formula    (IV)    R^(1-A)—X²  (IV)-   in which R^(1-A) is as defined above-   in the presence of a base and in the presence of a diluent, to give    the corresponding alkanoneanilines of the formula (X). [The reaction    conditions of the process (b) apply correspondingly.]

However, it is also possible to convert the alkanoneanilines of theformula (VII-a) according to process (f) according to the invention intothe corresponding aniline derivatives of the formula (III-a)

-   in which R² and R³ are as defined above,-   which are then, if appropriate, reacted with halides of the formula    (IV)    R^(1-A)—X²  (IV)-   in which R^(1-A) is as defined above-   in the presence of a base and in the presence of a diluent to give    the corresponding aniline derivatives of the formula (III). [The    reaction conditions of process (b) apply correspondingly.]

Aniline derivatives of the formula (III-b)

in which

-   a) R^(1-B) represents C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-Cycloalkyl;    C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13    fluorine, chlorine and/or bromine atoms; (C₁-C₈-alkyl)carbonyl,    (C₁-C₈-alkoxy)carbonyl, (C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,    (C₃-C₈-cycloalkyl)carbonyl; (C₁-C₆-haloalkyl)carbonyl,    (C₁-C₆-haloalkoxy)carbonyl, (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,    (C₃-C₈-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine,    chlorine and/or bromine atoms; or —C(═O)C(═O)R⁴, CONR⁵R⁶ or    —CH₂NR⁷R⁸, and    -   R^(3-B) represents hydrogen, halogen, C₁-C₈-alkyl,        C₁-C₈-haloalkyl,        or-   b) R^(1-B) represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;    C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13    fluorine, chlorine and/or bromine atoms; (C₁-C₈-alkyl)carbonyl,    (C₁-C₈-alkoxy)carbonyl, (C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,    (C₃-C₈-cycloalkyl)carbonyl; (C₁-C₆-haloalkyl)carbonyl,    (C₁-C₆-haloalkoxy)carbonyl, (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,    (C₃-C₈-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine,    chlorine and/or bromine atoms; or —C(═O)C(═O)R⁴, CONR⁵R⁶ or    —CH₂NR⁷R⁸ steht, and    -   R^(3-B) represents halogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl,        and-   R², R⁴, R⁵, R⁶, R⁷ and R⁸ are each as defined above-   are novel and also form part of the subject-matter of this    application.

The preferred, particularly preferred and very particularly preferredmeanings of R¹ and R³ apply correspondingly to R^(1-B) and R^(3-B),where in case a) R^(1-B) does in each case not represent hydrogen and incase b) R^(3-B) does not represent hydrogen. The preferred, particularlypreferred and very particularly preferred meanings of R², R⁴, R⁵, R⁶, R⁷and R⁸ apply likewise to the novel compounds of the formula (III-b).

Emphasis is given to compounds of the formula (III-b) in which R¹ and R²each represent hydrogen and R³ represents fluorine, chlorine, methyl,ethyl, trifluoromethyl and pentafluoroethyl.

Aniline derivatives of the formula (III) in which L represents L-1 arefurthermore obtained by

-   g) reacting aniline halides of the formula (XI)

-   -   in which    -   R^(1-A) and R² are as defined above and    -   X⁴ represents halogen    -   in a first step with alkynes of the formula (XII)

-   -   in which R³ is as defined above    -   in the presence of a catalyst, if appropriate in the presence of        a base and if appropriate in the presence of a diluent, and, in        a second step, hydrogenating the resulting alkyneanilines of the        formula (XIII)

-   -   in which R^(1-A), R² and R³ are as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a catalyst.

The formula (XI) provides a general definition of the aniline halidesrequired as starting materials for carrying out the process (g)according to the invention. In this formula (XI), R² preferably,particularly preferably and very particularly preferably has thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred for this radical. R^(1-A) has preferably,particularly preferably and very particularly preferably those meaningswhich have been mentioned in connection with the description of thecompounds of the formula (IV) as being preferred, particularly preferredand very particularly preferred, respectively, for this radical.

The aniline halides of the formula (XI) are known and/or can be obtainedby known processes, for example from the corresponding derivatives whichare unsubstituted at the nitrogen by reaction with the halides of theformula (IV).

The formula (XII) provides a general definition of the alkynesfurthermore required as starting materials for carrying out the process(g) according to the invention. In this formula (XII), R³ preferably,particularly preferably and very particularly preferably has thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for this radical.

The alkynes of the formula (XII) are known.

The formula (XIII) provides a general definition of the alkyneanilineswhich are intermediates obtained when carrying out the process (g)according to the invention. In this formula (XIII), R² and R³preferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for these radicals. R^(1-A) haspreferably, particularly preferably and very particularly preferablythose meanings which have been mentioned in connection with thedescription of the compounds of the formula (IV) as being preferred,particularly preferred and very particularly preferred, respectively,for this radical.

Some of the alkyneanilines of the formula (XIII) are known. They areobtained by process (g) according to the invention.

If aniline derivatives of the formula (III) in which R¹ representshydrogen are to be obtained, R^(1-A) is chosen such that it acts as aprotective group which, after process (g) according to the invention,can be removed by customary methods.

The aniline derivatives of the formula (III) in which L represents L-2,L-3 or L-4 are known and/or can be obtained by known processes (cf., forexample, EP-A 1 036 793 and EP-A 0 737 682).

Aniline derivatives of the formula (III) in which L represents L-2, L-3or L-4 and R¹ does not represent hydrogen can be obtained by reactinganilines of the formula (III-c)

in which

-   L¹ represents L-2, L-3 or L-4 and-   L-2, L-3, L-4 und R³ are as defined above-   with halides of the formula (IV)    R^(1-A)—X²  (IV)-   in which R^(1-A) and X² are as defined above-   in the presence of a base and in the presence of a diluent. [The    reaction conditions of process (b) apply correspondingly.]    Process (b)

Using5-fluoro-1,3-dimethyl-N-[2-(3-methylbutyl)phenyl]-1H-pyrazole-4-carboxamideand ethyl chloro(oxo)acetate as starting materials, the course of theprocess (b) according to the invention can be illustrated by thefollowing formula scheme:

The formula (I-a) provides a general definition of theisopentylcarboxanilides required as starting materials for carrying outthe process (b) according to the invention. In this formula (I-a), R²,R³ and A preferably, particularly preferably and very particularlypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferredand very particularly preferred, respectively, for these radicals.

The isopentylcarboxanilides of the formula (I-a) are also compoundsaccording to the invention and also form part of the subject-matter ofthis application. They can be obtained by one of processes (a), (c), (d)or (e) according to the invention (where R¹=hydrogen).

The formula (IV) provides a general definition of the halidesfurthermore required as starting materials for carrying out the process(b) according to the invention.

-   R^(1-A) preferably represents C₁-C₆-alkyl, C₁-C₄-alkylsulphinyl,    C₁-C₄-alkylsulphonyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-Cycloalkyl;    C₁-C₄-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    halo-C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13    fluorine, chlorine and/or bromine atoms;    -   (C₁-C₆-alkyl)carbonyl, (C₁-C₄-alkoxy)carbonyl,        (C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl, (C₃-C₆-cycloalkyl)carbonyl;        (C₁-C₄-haloalkyl)carbonyl, (C₁-C₄-haloalkoxy)carbonyl,        (halo-C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl,        (C₃-C₆-halocycloalkyl)carbonyl having in each case 1 to 9        fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R⁴,        —CONR⁵R⁶ or —CH₂NR⁷R⁸.-   R^(1-A) particularly preferably represents methyl, ethyl, n- or    isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl,    methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-,    sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or    isopropylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl,    methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl,    cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl,    trifluoroethyl, difluoromethylthio, difluorochloromethylthio,    trifluoromethylthio, trifluoromethylsulphinyl,    trifluoromethylsulphonyl, trifluoromethoxymethyl; formyl, —CH₂—CHO,    —(CH₂)₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂,    —(CH₂)₂—CO—CH₃, —(CH₂)₂—CO—CH₂CH₃, —(CH₂)₂—CO—CH(CH₃)₂, —CH₂—CO₂CH₃,    —CH₂—CO₂CH₂CH₃, —CH₂—CO₂CH(CH₃)₂, —(CH₂)₂—CO₂CH₃, —(CH₂)₂—CO₂CH₂CH₃,    —(CH₂)₂—CO₂CH(CH₃)₂, —CH₂—CO—CF₃, —CH₂—CO—CCl₃, —CH₂—CO—CH₂CF₃,    —CH₂—CO—CH₂CCl₃, —(CH₂)₂—CO—CH₂CF₃, —(CH₂)₂—CO—CH₂CCl₃,    —CH₂—CO₂CH₂CF₃, —CH₂—CO₂CF₂CF₃, —CH₂—CO₂CH₂CCl₃, —CH₂—CO₂CCl₂CCl₃,    —(CH₂)₂—CO₂CH₂CF₃, —(CH₂)₂—CO₂CF₂CF₃, —(CH₂)₂—CO₂CH₂CCl₃,    —(CH₂)₂—CO₂CCl₂CCl₃;    -   methylcarbonyl, ethylcarbonyl, n-propylcarbonyl,        isopropylcarbonyl, tert-butylcarbonyl, methoxycarbonyl,        ethoxycarbonyl, tert-butoxycarbonyl, cyclopropylcarbonyl;        trifluoromethylcarbonyl, trifluoromethoxycarbonyl, or        —C(═O)C(═O)R⁵, —CONR⁶R⁷ or —CH₂NR⁸R⁹.-   R^(1-A) very particularly preferably represents methyl,    methoxymethyl, formyl, —CH₂—CHO, —(CH₂)₂—CHO, —CH₂—CO—CH₃,    —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂, —C(═O)CHO, —C(═O)C(═O)CH₃,    —C(═O)C(═O)CH₂OCH₃, —C(═O)CO₂CH₃, —C(═O)CO₂CH₂CH₃.-   X² preferably represents chlorine or bromine.

Halides of the formula (IV) are known.

Process (c)

Using 2-Iodo-N-[2-(3-methylbutanoyl)phenyl]benzamide as startingmaterial, and hydrazine and a base, the course of the process (c)according to the invention can be illustrated by the formula schemebelow:

The formula (V) provides a general definition of the isopentonederivatives required as starting materials for carrying out the process(c) according to the invention. In this formula (V), R¹, R², R³ and Apreferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for these radicals.

The isopentone derivatives of the formula (V) are novel. They areobtained by

-   h) reacting carboxylic acid derivatives of the formula (II)

-   -   in which    -   A is as defined above    -   X¹ represents halogen or hydroxyl    -   with alkanoneanilines of the formula (X)

-   -   in which R¹, R² and R³ are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of a condensing agent, if appropriate in the        presence of an acid binder and if appropriate in the presence of        a diluent.

The carboxylic acid derivatives of the formula (II) required as startingmaterials for carrying out the process (h) according to the inventionhave already been described in connection with process (a) according tothe invention.

The alkanoneanilines of the formula (X) furthermore required as startingmaterial for carrying out the process (h) according to the inventionhave already been described in connection with process (f) according tothe invention.

Process (d)

UsingN-{2-[3,3-dimethylbut-1-en-1-yl]phenyl}-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideas starting material and hydrogen, the course of the process (d)according to the invention can be illustrated by the formula schemebelow:

The formula (VI) provides a general definition of the isopentenederivatives required as starting materials for carrying out the process(d) according to the invention. In this formula (VI), R¹, R², R³ and Apreferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred for these radicals.

The isopentene derivatives of the formula (VI) are novel. They areobtained by

-   j) reacting carboxamides of the formula (XIV)

-   -   in which    -   R¹, R² and A are as defined above and    -   X⁵ represents chlorine, bromine, iodine or —OSO₂CF₃    -   with alkenes of the formula (XV)

-   -   in which R³ is as defined above    -   in the presence of a catalyst, if appropriate in the presence of        a base and if appropriate in the presence of a diluent.

The formula (XIV) provides a general definition of the carboxamidesfurthermore required as starting materials for carrying out the process(j) according to the invention. In this formula (XIV), R¹, R² and Apreferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively; for these radicals. X⁵ preferablyrepresents bromine or —OSO₂CF₃.

The carboxamides of the formula (XIV) are novel or can be obtained byknown methods (cf. WO 02/08195 and WO 02/08197).

The formula (XV) provides a general definition of the alkenesfurthermore required as starting materials for carrying out the process(j) according to the invention. In this formula (XV), R³ preferably,particularly preferably and very particularly preferably has thosemeanings which have already been mentioned in the description of thecompounds of the formula (I) according to the invention as beingpreferred, particularly preferred and very particularly preferred,respectively, for this radical.

The alkenes of the formula (XV) are known.

Process (e)

UsingN-[2-3,3-dimethylbut-1-yn-1-yl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideas starting material and hydrogen, the course of the process (e)according to the invention can be illustrated by the formula schemebelow:

The formula (VII) provides a general definition of the isopentynederivatives required as starting materials for carrying out the process(e) according to the invention. In this formula (VII), R¹, R², R³ and Apreferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred for these radicals.

The isopentyne derivatives of the formula (VII) in which A does notrepresent A1 are novel. The isopentyne derivatives of the formula (VII)are obtained by

-   k) reacting carboxamides of the formula (XIV)

-   -   in which    -   R¹, R² and A are as defined above and    -   X⁵ represents chlorine, bromine, iodine or —OSO₂CF₃,    -   with alkynes of the formula (XII)

-   -   in which R³ is as defined above    -   in the presence of a catalyst, if appropriate in the presence of        a base and if appropriate in the presence of a diluent.    -   The carboxamides of the formula (XIV) required as starting        materials for carrying out the process (k) according to the        invention have already been described in connection with the        process (j) according to the invention.    -   The alkynes of the formula (XII) furthermore required as        starting materials for carrying out the process (k) according to        the invention have already been described in connection with the        process (g) according to the invention.        Reaction Conditions

Suitable diluents for carrying out the process (a) and (h) according tothe invention are all inert organic solvents. These preferably includealiphatic, alicyclic or aromatic hydrocarbons, such as, for example,petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether,methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole, or amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide.

The processes (a) and (h) according to the invention are, ifappropriate, carried out in the presence of a suitable acid acceptor.Suitable acid acceptors are all customary inorganic or organic bases.These preferably include alkaline earth metal or alkali metal hydrides,hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates,such as, for example, sodium hydride, sodium amide, sodium methoxide,sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassiumhydroxide, ammonium hydroxide, sodium acetate, potassium acetate,calcium acetate, ammonium acetate, sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate or ammoniumcarbonate, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

The processes (a) and (h) according to the invention are, ifappropriate, carried out in the presence of a suitable condensing agent.Suitable condensing agents are all condensing agents customarily usedfor such amidation reactions. Acid halide formers, such as phosgene,phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride,phosphorus oxychloride or thionyl chloride; anhydride formers, such asethyl chloroformate, methyl chloroformate, isopropyl chloroformate,isobutyl chloroformate or methylsulphonyl chloride; carbodiimides, suchas N,N′-dicyclohexylcarbodiimide (DCC), or other customary condensingagents, such as phosphorus pentoxide, polyphosphoric acid,N,N′-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline(EEDQ), triphenylphosphine/carbon tetrachloride orbromotripyrrolidinophosphonium hexafluorophosphate may be mentioned byway of example.

The processes (a) and (h) according to the invention are, ifappropriate, carried out in the presence of a catalyst. Examples whichmay be mentioned are 4-dimethylaminopyridine, 1-hydroxybenzotriazole ordimethylformamide.

When carrying out the processes (a) and (h) according to the invention,the reaction temperatures can be varied within a relatively wide range.In general, the processes are carried out at temperatures of from 0° C.to 150° C., preferably at temperatures of from 0° C. to 80° C.

For carrying out the process (a) according to the invention forpreparing the compounds of the formula (I), in general from 0.2 to 5mol, preferably from 0.5 to 2 mol, of aniline derivative of the formula(III) are employed per mole of the carboxylic acid derivative of theformula (II).

For carrying out the process (h) according to the invention forpreparing the compounds of the formula (V), in general from 0.2 to 5mol, preferably from 0.5 to 2 mol, of alkanoneaniline of the formula (X)are employed per mole of the carboxylic acid derivative of the formula(II).

Suitable diluents for carrying out the process (b) according to theinvention are all inert organic solvents. These preferably includealiphatic, alicyclic or aromatic hydrocarbons, such as, for example,petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl tert-butylether, methyl tert-amyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide.

The process (b) according to the invention is carried out in thepresence of a base. Suitable bases are all customary inorganic ororganic bases. These preferably include alkaline earth metal or alkalimetal hydrides, hydroxides, amides, alkoxides, acetates, carbonates orbicarbonates, such as, for example, sodium hydride, sodium amide, sodiummethoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide,potassium hydroxide, ammonium hydroxide, sodium acetate, potassiumacetate, calcium acetate, ammonium acetate, sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate or caesiumcarbonate, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the process (b) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures of from 0° C. to150° C., preferably at temperatures of from 20° C. to 110° C.

For carrying out the process (b) according to the invention forpreparing the compounds of the formula (I), in general from 0.2 to 5mol, preferably from 0.5 to 2 mol, of halide of the formula (IV) areemployed per mole of the isopentylcarboxanilide of the formula (I-a).

Suitable diluents for carrying out the process (c) according to theinvention and the second step of process (f) are all inert organicsolvents. These preferably include aliphatic, alicyclic or aromatichydrocarbons, such as, for example, petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin;halogenated hydrocarbons, such as, for example, chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichloroethane or trichloroethane; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;ketones, such as acetone, butanone, methyl isobutyl ketone orcyclohexanone; nitriles, such as acetonitrile, propionitrile, n- ori-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; sulphoxides, such as dimethyl sulphoxide;sulphones, such as sulpholane; alcohols, such as methanol, ethanol, n-or i-propanol, n-, i-, sec- or tert-butanol, ethanediol,propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycolmonomethyl ether, diethylene glycol monoethyl ether, triethylene glycol,mixtures thereof with water or pure water.

The process (c) according to the invention and the second step ofprocess (f) are carried out in the presence of a base. Preferred basesare alkaline earth metal or alkali metal hydroxides, such as, forexample, sodium hydroxide, potassium hydroxide, ammonium hydroxide.

When carrying out the process (c) according to the invention and thesecond step of process (f), the reaction temperatures can be variedwithin a relatively wide range. In general, the reactions are carriedout at temperatures of from 100° C. to 300° C., preferably attemperatures of from 150° C. to 250° C.

When carrying out the process (c) according to the invention forpreparing the compounds of the formula (I), in general from 0.2 to 5mol, preferably from 0.5 to 3 mol, of hydrazine (or hydrazine hydrate)are employed per mole of the isopentone derivative of the formula (V).

For carrying out the second step of process (f) for preparing thecompounds of the aniline derivatives of the formula (M), in general from0.2 to 5 mol, preferably from 0.5 to 3 mol, of hydrazine (or hydrazinehydrate) are employed per mole of the alkanoneaniline of the formula(X).

Suitable diluents for carrying out the processes (d) and (e) accordingto the invention and the second step of process (g) are all inertorganic solvents. These preferably include aliphatic or alicyclichydrocarbons, such as, for example, petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane or decalin; ethers, such as diethylether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether,dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane;alcohols, such as methanol, ethanol, n- or isopropanol, n-, iso-, sec-or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol,methoxyethanol, diethylene glycol monomethyl ether, diethylene glycolmonoethyl ether, mixtures thereof with water or pure water.

The processes (d) and (e) according to the invention and the second stepof process (g) are carried out in the presence of a catalyst. Suitablecatalysts are all catalysts which are usually used for hydrogenation.The following may be mentioned by way of example: Raney nickel,palladium or platinum, if appropriate on a support, such as, forexample, activated carbon.

Instead of in the presence of hydrogen in combination with a catalyst,the hydrogenation in the processes (d) and (e) according to theinvention and in the second step of process (g) can also be carried outin the presence of triethylsilane.

When carrying out the processes (d) and (e) according to the inventionand the second step of process (g), the reaction temperatures can bevaried within a relatively wide range. In general, the reactions arecarried out at temperatures of from 0° C. to 150° C., preferably attemperatures of from 20° C. to 100° C.

The processes (d) and (e) according to the invention and the second stepof process (g) are carried out under a hydrogen pressure between 0.5 and200 bar, preferably between 2 and 50 bar, particularly preferablybetween 3 and 10 bar.

Suitable diluents for carrying out the first step of process (f) are allinert organic solvents. These preferably include aliphatic or alicyclichydrocarbons, such as, for example, petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane or decalin; ethers, such as diethylether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether,dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane.

When carrying out the first step of process (f), the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures from 0° C. to 200° C.,preferably at temperatures of from 20° C. to 150° C.

For carrying out the first step of process (f) for preparing thecompounds of the alkanoneanilines of the formula (X), in general from0.2 to 5 mol, preferably from 0.5 to 3 mol, of Grignard reagent of theformula (IX) are employed per mole of the cyanoaniline of the formula(VIII).

Suitable diluents for carrying out the first step of process (g) and theprocesses (j) and (k) according to the invention are all inert organicsolvents. These preferably include nitriles, such as acetonitrile,propionitrile, n- or i-butyronitrile or benzonitrile, or amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; ethers, such asdiethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or1,2-diethoxyethane.

The first step of process (g) and the processes (j) and (k) according tothe invention are, if appropriate, carried out in the presence of asuitable acid acceptor. Suitable acid acceptors are all customaryinorganic or organic bases. These preferably include alkaline earthmetal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates,carbonates or bicarbonates, such as, for example, sodium hydride, sodiumamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide,sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodiumacetate, potassium acetate, calcium acetate, ammonium acetate, sodiumcarbonate, potassium carbonate, potassium bicarbonate, sodiumbicarbonate or ammonium carbonate, and also tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

The first step of process (g) and the processes (j) and (k) according tothe invention are carried out in the presence of one or more catalysts.

Suitable catalysts are in particular palladium salts or complexes.Suitable for this purpose are, preferably, palladium chloride, palladiumacetate, tetrakis(triphenylphosphine)palladium orbis(triphenylphosphine)palladium dichloride. It is also possible togenerate a palladium complex in the reaction mixture by adding apalladium salt and a complex ligand separately to the reaction.

Suitable ligands are, preferably, organophosphorus compounds. Thefollowing may be mentioned by way of example: triphenylphosphine,tri-o-tolylphosphine, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl,dicyclohexylphosphinebiphenyl, 1,4-bis(diphenylphosphino)butane,bisdiphenylphosphinoferrocene, di-(tert-butylphosphino)biphenyl,di(cyclohexylphosphino)biphenyl,2-dicyclohexylphosphino-2′-N,N-dimethylaminobiphenyl,tricyclohexylphosphine, tri-tert.-butylphosphine. However, ligands mayalso be dispensed with.

The first step of process (g) and the processes (j) and (k) according tothe invention are furthermore, if appropriate, carried out in thepresence of a further metal salt, such as copper salts, for examplecopper(I) iodide.

When carrying out the first step of process (g) and the processes (j)and (k) according to the invention, the reaction temperatures can bevaried within a relatively wide range. In general, the reactions arecarried out at temperatures of from 20° C. to 180° C., preferably attemperatures of from 50° C. to 150° C.

For carrying out the first step of process (g) for preparing the anilinederivatives of the formula (III), in general from 1 to 5 mol, preferablyfrom 1 to 3 mol, of alkyne of the formula (XII) are employed per mole ofthe aniline halide of the formula (XI).

For carrying out the process (j) according to the invention forpreparing the isopentene derivatives of the formula (VI), in generalfrom 1 to 5 mol, preferably from 1 to 3 mol, of alkene of the formula(XV) are employed per mole of the carboxamide of the formula (XIV).

For carrying out the process (k) according to the invention forpreparing the isopentyne derivatives of the formula (VII), in generalfrom 1 to 5 mol, preferably from 1 to 3 mol, of alkyne of the formula(XII) are employed per mole of the carboxamide of the formula (XIV).

Unless stated otherwise, all processes according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to operate under elevated or reduced pressure—in generalbetween 0.1 bar and 10 bar.

The substances according to the invention have potent microbial activityand can be employed for controlling unwanted microorganisms, such asfungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

-   Xanthomonas species, such as, for example, Xanthomonas campestris    pv. oryzae;-   Pseudomonas species, such as, for example, Pseudomonas syringae pv.    lachrymans;-   Erwinia species, such as, for example, Erwinia amylovora;-   Pythium species, such as, for example, Pythium ultimum;-   Phytophthora species, such as, for example, Phytophthora infestans;-   Pseudoperonospora species, such as, for example, Pseudoperonospora    humuli or Pseudoperonospora cubensis;-   Plasmopara species, such as, for example, Plasmopara viticola;-   Bremia species, such as, for example, Bremia lactucae;-   Peronospora species, such as, for example, Peronospora pisi or P.    brassicae;-   Erysiphe species, such as, for example, Erysiphe graminis;-   Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;-   Podosphaera species, such as, for example, Podosphaera leucotricha;-   Venturia species, such as, for example, Venturia inaequalis;-   Pyrenophora species, such as, for example, Pyrenophora teres or P.    graminea-   (conidia form: Drechslera, syn: Helminthosporium);-   Cochliobolus species, such as, for example, Cochliobolus sativus-   (conidia form: Drechslera, syn: Helminthosporium);-   Uromyces species, such as, for example, Uromyces appendiculatus;-   Puccinia species, such as, for example, Puccinia recondita;-   Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;-   Tilletia species, such as, for example, Tilletia caries;-   Ustilago species, such as, for example, Ustilago nuda or Ustilago    avenae;-   Pellicularia species, such as, for example, Pellicularia sasakii;-   Pyricularia species, such as, for example, Pyricularia oryzae;-   Fusarium species, such as, for example, Fusarium culmorum;-   Botrytis species, such as, for example, Botrytis cinerea;-   Septoria species, such as, for example, Septoria nodorum;-   Leptosphaeria species, such as, for example, Leptosphaeria nodorum;-   Cercospora species, such as, for example, Cercospora canescens;-   Alternaria species, such as, for example, Alternaria brassicae; and-   Pseudocercosporella species, such as, for example,    Pseudocercosporella herpotrichoides,-   Rhizoctonia species, such as, for example, Rhizoctonia solani.

The active compounds according to the invention also show a stronginvigorating action in plants. Accordingly, they are suitable formobilizing the internal defences of the plant against attack by unwantedmicroorganisms.

In the present context, plant-invigorating (resistance-inducing)compounds are to be understood as meaning substances which are capableof stimulating the defence system of plants such that, when the treatedplants are subsequently inoculated with unwanted microorganisms, theydisplay substantial resistance to these microorganisms.

In the present case, unwanted microorganisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. The compoundsaccording to the invention can thus be used to protect plants within acertain period of time after treatment against attack by the pathogensmentioned. The period of time for which this protection is achievedgenerally extends for 1 to 10 days, preferably 1 to 7 days, from thetreatment of the plants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

Here, the active compounds according to the invention can be used withparticularly good results for controlling cereal diseases, such as, forexample, against Puccinia species, and of diseases in viticulture and inthe cultivation of fruits and vegetables, such as, for example, againstbotrytis, Venturia or Alternaria species.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

If appropriate, the active compounds according to the invention can, atcertain concentrations and application rates, also be employed asherbicides, for regulating plant growth and for controlling animalpests. If appropriate, they can also be used as intermediates orprecursors in the synthesis of other active compounds.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations, such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders' certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested material and vegetative and generative propagation material,for example seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormultilayer coating.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, unwanted microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be tackifiers, sizes, paper and board, textiles,leather, wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably tackifiers, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes) and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

-   Alternaria, such as Alternaria tenuis,-   Aspergillus, such as Aspergillus niger,-   Chaetomium, such as Chaetomium globosum,-   Coniophora, such as Coniophora puetana,-   Lentinus, such as Lentinus tigrinus,-   Penicillium, such as Penicillium glaucum,-   Polyporus, such as Polyporus versicolor,-   Aureobasidium, such as Aureobasidium pullulans,-   Sclerophoma, such as Sclerophoma pityophila,-   Trichoderma, such as Trichoderma viride,-   Escherichia, such as Escherichia coli,-   Pseudomonas, such as Pseudomonas aeruginosa, and-   Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can, as such or in theirformulations, also be used in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Suitable mixing components are, for example, the following compounds:

Fungicides:

2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-S-methyl;aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium; andoprim;anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl;benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos;binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole;bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin;captafol; captan; carbendazim; carboxin; carpropamid; carvone;chinomethionat; chlobenthiazone; chlorfenazole; chloroneb;chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid;cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb;dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine;dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol;dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap;diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon;edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram;fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin;fenpropimorph; ferbam; fluazinam; flubenzinine; fludioxonil; flumetover;flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol;flusilazole; flusulphamide; flutolanil; flutriafol; folpet; fosetyl-Al;fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil;furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazole;imazalil; imibenconazole; iminoctadine triacetate; iminoctadinetris(albesil); iodocarb; ipconazole; iprobenfos; iprodione;iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin;kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil;metalaxyl; metalaxyl-M; metconazole; methasulphocarb; methfuroxam;metiram; metominostrobin; metsulphovax; mildiomycin; myclobutanil;myclozolin; natamycin; nicobifen; nitrothal-isopropyl; noviflumuron;nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;oxycarboxin; oxyfenthiin; paclobutrazole; pefurazoate; penconazole;pencycuron; phosdiphen; phthalide; picoxystrobin; piperalin; polyoxins;polyoxorim; probenazole; prochloraz; procymidone; propamocarb;propanosine-sodium; propiconazole; propineb; proquinazid;prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil;pyroqui-Ion; pyroxyfur; pyrrolenitrine; quinconazole; quinoxyfen;quintozene; simeconazole; spiroxamine; sulphur; tebuconazole;tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole;thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid;tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil;triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobin;triflumizole; triforine; triticonazole; uniconazole; validamycin A;vinclozolin; zineb; ziram; zoxamide;(2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]-butanamide;1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine;2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;3,4,5-trichloro-2,6-pyridinedicarbonitrile; actinovate;cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol; methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;monopotassium carbonate;N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide;N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro[4.5]decane-3-amine; sodiumtetrathiocarbonate; and copper salts and preparations, such as Bordeauxmixture; copper hydroxide; copper naphthenate; copper oxychloride;copper sulphate; cufraneb; copper oxide; mancopper; oxine-copper.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole,acrinatin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb,aldoxycarb, allethrin, allethrin 1R-isomers, alpha-cypermethrin(alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ-60541,azadirachtin, azamethiphos, azinphos-methyl, azinphos-ethyl,azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillusthuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821,baculoviruses, Beauveria bassiana, Beauveria tenella, benclothiaz,bendiocarb, benfuracarb, bensultap, benzoximate, beta-cyfluthrin,beta-cypermethrin, bifenazate, bifenthrin, binapacryl, bioallethrin,bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin,bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl,bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505, bufencarb,buprofezin, butathiofos, butocarboxim, butoxycarboxim, butylpyridaben,cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion,carbosulphan, cartap, CGA-50439, chinomethionat, chlordane,chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr,chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate,chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl),chlovaporthrin, chromafenozide, cis-cyperrethrin, cis-resmethrin,cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidin,clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene,cycloprothrin, Cydia pomonella, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyphenothrin (1R-trans-isomer), cyromazine, DDT,deltamethrin, demeton-S-methyl, demeton-S-methylsulphone, diafenthiuron,dialifos, diazinon, dichlofenthion, dichlorvos, dicofol, dicrotophos,dicyclanil, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos,dinobuton, dinocap, dinotefuran, diofenolan, disulphoton,docusat-sodium, dofenapyn, DOWCO-439, eflusilanate, emamectin,emamectin-benzoate, empenthrin (1R-isomer), endosulphan, Entomopthoraspp., EPN, esfenvalerate, ethiofencarb, ethiprole, ethion, ethoprophos,etofenprox, etoxazole, etrimfos, famphur, fenamiphos, fenazaquin,fenbutatin oxide, fenfluthrin, fenitrothion, fenobucarb, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fensulphothion, fenthion, fentrifanil, fenvalerate,fipronil, flonicamid, fluacrypyrim, fluazuron, flubenzimine,flubrocythrinate, flucycloxuron, flucythrinate, flufenerim,flufenoxuron, flufenprox, flumethrin, flupyrazofos, flutenzin(flufenzine), fluvalinate, fonofos, formetanate, formothion,fosmethilan, fosthiazate, fubfenprox (fluproxyfen), furathiocarb,gamma-cyhalothrin, gamma-HCH, gossyplure, grandlure, granulosis viruses,halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron,hexythiazox, hydramethylnone, hydroprene, IKA-2002, imidacloprid,imiprothrin, indoxacarb, iodofenphos, iprobenfos, isazofos, isofenphos,isoprocarb, isoxathion, ivermectin, japonilure, kadethrin, nuclearpolyhedrosis viruses, kinoprene, lambda-cyhalothrin, lindane, lufenuron,malathion, mecarbam, mesulphenfos, metaldehyde, metam-sodium,methacrifos, methamidophos, Metharhizium anisopliae, Metharhiziumflavoviride, methidathion, methiocarb, methomyl, methoprene,methoxychlor, methoxyfenozide, metofluthrin, metolcarb, metoxadiazone,mevinphos, milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos,moxidectin, MTI-800, naled, NC-104, NC-170, NC-184, NC-194, NC-196,niclosamide, nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101,NNI-0250, NNI-9768, novaluron, noviflumuron, OK-5101, OK-5201, OK-9601,OK-9602, OK-9701, OK-9802, omethoate, oxamyl, oxydemeton-methyl,Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl),permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-transisomer), phenthoate, phorate, phosalone, phosmet, phosphamidon,phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimiphos-methyl,pirimiphos-ethyl, potassium oleate, prallethrin, profenofos,profluthrin, promecarb, propaphos, propargite, propetamphos, propoxur,prothiofos, prothoate, protrifenbute, pymetrozine, pyraclofos,pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyridaphenthion,pyridathion, pyrimidifen, pyriproxyfen, quinalphos, resmethrin, RH-5849,ribavirin, RU-12457, RU-15525, S-421, S-1833, salithion, sebufos,SI-0009, silafluofen, spinosad, spirodiclofen, spiromesifen,sulphluramid, sulphotep, sulprofos, SZI-121, tau-fluvalinate,tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin,temephos, temivinphos, terbam, terbufos, tetrachlorvinphos, tetradifon,tetramethrin, tetramethrin (1R-isomer), tetrasul, theta-cypermethrin,thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclamhydrogenoxalate, thiodicarb, thiofanox, thiometon, thiosultap-sodium,thuringiensin, tolfenpyrad, tralocythrin, tralomethrin, transfluthrin,triarathene, triazamate, triazophos, triazuron, trichlophenidine,trichlorfon, Trichoderma atroviride, triflumuron, trimethacarb,vamidothion, vaniliprole, verbutin, Verticillium lecanii, WL-108477,WL-40027, YI-5201, YI-5301, YI-5302, XMC, xylylcarb, ZA-3274,zeta-cypermethrin, zolaprofos, ZXI-8901, the compound 3-methylphenylpropylcarbamate (tsumacide Z), the compound3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane-3-carbonitrile(CAS-Reg. No. 185982-80-3) and the corresponding 3-endo-isomer (CAS-Reg.No. 185984-60-5) (cf. WO-96/37494, WO-98/25923), and preparations whichcomprise insecticidally active plant extracts, nematodes, fungi orviruses.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, safeners and/or semiochemicals isalso possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida speciessuch as Candida albicans, Candida glabrata) and Epidermophytonfloccosum, Aspergillus species such as Aspergillus niger and Aspergillusfumigatus, Trichophyton species such as Trichophyton mentagrophytes,Microsporon species such as Microsporon canis and audouinii. The list ofthese fungi by no means limits the mycotic spectrum which can becovered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5,000 g/ha.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof, are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, varieties, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, cotton, tobacco and oilseedrape. Traits that are emphasized are in particular increased defence ofthe plants against insects, arachnids, nematodes and slugs and snails bytoxins formed in the plants, in particular those formed in the plants bythe genetic material from Bacillus thuringiensis (for example by thegenes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c,Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelowreferred to as “Bt plants”). Traits that are also particularlyemphasized are the increased defence of the plants against fungi,bacteria and viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins. Traits that are furthermore particularlyemphasized are the increased tolerance of the plants to certainherbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinotricin (for example the “PAT”gene). The genes which impart the desired traits in question can also bepresent in combination with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize varieties,cotton varieties, soya bean varieties and potato varieties which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are sold under the tradenames Roundup Ready® (tolerance to glyphosate, for example maize,cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulphonylureas, for example maize). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned also include the varieties sold under the nameClearfield® (for example maize). Of course, these statements also applyto plant cultivars which have these genetic traits or genetic traitsstill to be developed, and which will be developed and/or marketed inthe future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

326.5 mg (2.0 mmol) of [2-(3-methylbutyl)phenyl]amine (III-1) are addedto a solution comprising 388.5 mg (2.2 mmol) of5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride and 0.45 ml (3.2mmol) of triethylamine in 20 ml of tetrahydrofuran. The reactionsolution is stirred at 60° C. for 90 min, filtered through silica geland concentrated. Column chromatography (cyclohexane/ethyl acetategradient) gives 592 mg (98% of theory) of5-fluoro-1,3-dimethyl-N-[2-(3-methylbutyl)phenyl]-1H-pyrazole-4-carboxamideof logP (pH 2.3)=3.12.

The compounds of the formula (I) listed in Table 1 below are obtainedanalogously to Example 1 and in accordance with the instructions in thegeneral descriptions of the processes.

TABLE 1 (I)

Ex. R¹ R² R³ A logP 2 H H CH₃

3.42 3 H H CH₃

4.14 4 H H H

3.90 5 H H CH₃

4.13 6 H H H

3.87 7 H H CH₃

4.15 8 H H H

3.78 9 H H H

3.76 10 H H H

3.68 11 H H CH₃

3.28 12 H H CH₃

3.91 13 H 4-Cl C₂H₅

4.96 14 H 4-Cl C₂H₅

5.02 15 H 4-Cl C₂H₅

4.29 16 H H CH₃

4.54 17 H H C₂H₅

3.68 18 H H C₂H₅

3.59 19 H 4-Cl C₂H₅

4.10 20 H 4-F CH₃

3.34 21 H 4-F CH₃

4.14 22 H 4-F CH₃

3.34 23 H 4-F CH₃

3.57 24 H 4-F CH₃

4.05Preparation of Starting Materials of the Formula (III)

Example (III-1)

A solution comprising 8.0 g (0.045 mol) of1-(2-aminophenyl)-3-methylbutan-1-one (X-1), 6.8 g (0.135 mol) ofhydrazine hydrate and 7.6 g (0.135 mol) of potassium hydroxide in 90 mlof triethylene glycol is heated at 210° C. for 6 h. For work-up, waterand ethyl acetate are added at room temperature. The organic phase isagain washed with water, dried over magnesium sulphate and concentratedunder reduced pressure. Purification by column chromatography(cyclohexane/ethyl acetate 3:1) gives 5.3 g (71.5% of theory) of[2-(3-methylbutyl)-phenyl]amine.

Example (III-2)

3.23 g (15 mmol) of N-[2-(3,3-dimethylbut-1-ynyl)phenyl]acetamide(XIII-1) were initially charged in 40 ml of methanol. 0.5 g ofpalladium-on-carbon (5%) was added, and the mixture is then hydrogenatedin an autoclave at a hydrogen pressure of 4 bar for 20 h. Removal of thecatalyst and the solvent gave 3.1 g (94% of theory) ofN-[2-(3,3-dimethylbutyl)phenyl]acetamide of logP (pH 2.3)=2.69.

Example (III-3)

0.5 g (2.3 mmol) of N-[2-(3,3-dimethylbutyl)phenyl]acetamide (III-2)were stirred in 20 ml of 2N hydrochloric acid at 100° C. for 5 h. Aftercooling, the mixture was extracted 3 times with in each case 20 ml ofethyl acetate. The organic phase was removed, dried over sodium sulphateand concentrated. This gave 390 mg (29% of theory) of2-(3,3-dimethylbutyl)phenylamine hydrochloride of logP (pH 2.3)=2.20.

Preparation of Starting Materials of the Formula (V)

Example (V-1)

At room temperature, 355.0 mg (2.0 mmol) of1-(2-aminophenyl)-3-methylbutan-1-one are added to a solution comprising388.5 mg (2.2 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonylchloride and 0.45 ml (3.2 mmol) of triethylamine in 20 ml oftetrahydrofuran. The reaction mixture is stirred at 60° C. for 1.5 h,filtered through silica gel and concentrated. Column chromatography(cyclohexane/ethyl acetate: 3/1) gives 577.7 mg (1.8 mmol, 88% oftheory) ofN-[2-(3-methylbutyryl)phenyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideof logP (pH=2.3)=3.42.

The compounds of the formula (V) listed in Table 2 below are obtainedanalogously to Example (V-1) and in accordance with the instructions inthe general descriptions of the processes.

TABLE 2 (V)

Ex. R¹ R² R³ A logP V-2 H H H

4.30 V-3 H H H

4.33 V-4 H H H

4.53 V-5 H H H

4.35 V-6 H H H

4.30 V-7 H H H

4.44Preparation of Starting Materials of the Formula (VII)

Example (VII-1)

190 mg (1.0 mmol) of 2-trifluoromethylbenzoic acid, 178 mg (0.83 mmol)of 2-(3,3-dimethyl-but-1-ynyl)phenylamine, 215 mg (1.67 mmol) ofN,N-diisopropylethylamine and 583 mg (1.25 mmol) of PyBrOP in 8 ml ofacetonitrile were stirred at room temperature for 4 days. 10 ml of ethylacetate/water 1:1 were added to the mixture and the organic phase wasseparated off and washed with 10 ml of saturated ammonium chloridesolution and subsequently with 10 ml of water. Separation, concentrationand drying of the organic phase gave 950 mg of crude product.Column-chromatographic purification on silica gel 60 (petroleumether/ethyl acetate 10:1→ethyl acetate) gave 110 mg ofN-[2-(3,3-dimethylbut-1-ynyl)phenyl]-2-trifluoromethylbenzamide [logP(pH 2.3)=4.55].

The compounds of the formula (VII) listed in Table 3 below are obtainedanalogously to Example (VII-1) and in accordance with the instructionsin the general descriptions of the processes.

TABLE 3 (VII)

Ex. R¹ R² R³ A logP VII-2 H H CH₃

4.73 VII-3 H H CH₃

3.75 VII-4 H H CH₃

4.52 VII-5 H H CH₃

4.17Preparation of Starting Materials of the Formula (X)

Example (X-1)

At reflux, a solution of 29.5 g (0.25 mol) of anthranilonitrile in 150ml of tetrahydrofuran is added dropwise to a suspension comprising 18.2g (0.75 mmol) of magnesium, 375 ml of a 2 M solution ofisobutylmagnesium bromide in tetrahydrofuran and 15 ml of diethyl ether.After 5 h of heating under reflux, 100 ml of water are, at 0° C., addedto the reaction mixture, and the pH is adjusted to 6 using hydrochloricacid. The organic phase is washed with water and dried over magnesiumsulphate. Concentration under reduced pressure and purification onsilica gel (mobile phase: petroleum ether/acetonitrile 95:5) gives 11.0g (25% of theory) of 1-(2-aminophenyl)-3-methylbutan-1-one of logP (pH2.3)=2.89.

Preparation of Starting Materials of the Formula (XIII)

Example (XIII-1)

Under argon, 25.7 g (120 mmol) of ortho-bromoacetanilide, 5.05 g (7.2mmol) of bis(triphenylphosphine)palladium(II) chloride and 1.37 g (7.2mmol) of copper(I) iodide were initially charged in 450 ml oftriethylamine. At room temperature, 17.8 g (180 mmol) of3,3-dimethyl-1-butyne were then added dropwise over a period of 10 min,and the mixture is stirred at 50° C. for 5 h. The reaction mixture waspoured into 2 l of water and extracted 3 times with in each case 250 mlof diethyl ether, and the extracts were dried over sodium sulphate andconcentrated. Column-chromatographic purification on silica gel 60 withmethylene chloride gave 25.9 g ofN-[2-(3,3-dimethylbut-1-ynyl)-phenyl]acetamide of logP (pH 2.3)=3.03.

The determination of the logP values given in preparation examples andtables above is carried out according to EEC-Directive 79/831 Annex V.A8by HPLC (High Performance Liquid Chromatography) on a reversed phasecolumn (C 18). Temperature: 43° C.

Determination is carried out in the acidic range at pH 2.3 using themobile phases 0.1% aqueous phosphoric acid and acetonitrile; lineargradient from 10% acetonitrile to 90% acetonitrile.

Calibration is carried out using unbranched alkan-2-ones (of 3 to 16carbon atoms) whose logP values are known (determination of the logPvalues by retention times using linear interpolation between twosuccessive alkanones).

The lambda-max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

Use Examples Example A

Podosphaera test (apple)/protective Solvents: 24.5 parts by weight ofacetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof compound is mixed with the stated amounts of solvents and emulsifier,and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rates. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of the apple mildew pathogen Podosphaeraleucotricha. The plants are then placed in a greenhouse at about 23° C.and a relative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE A Podosphaera test (apple)/protective Application rate Activecompound according of active Efficacy to the invention compound in g/hain %

100 100

100 100

100 99

100 97

100 99

100 100

100 100

100 100

Example B

Venturia test (apple)/protective Solvents: 24.5 parts by weight ofacetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rates. Afterthe spray coating has dried on, the plants are inoculated with anaqueous conidia suspension of the apple scab pathogen Venturiainaequalis and then remain in an incubation cabin at about 20° C. and100% relative atmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

TABLE B Venturia test (apple)/protective Application rate Activecompound according of active Efficacy to the invention compound in g/hain %

100 96

100 100

100 99

100 97

100 100

100 100

100 100

100 100

100 100

Example C

Botrytis test (bean)/protective Solvents: 24.5 parts by weight ofacetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rates. Afterthe spray coating has dried on, 2 small pieces of agar colonized byBotrytis cinerea are placed onto each leaf. The inoculated plants areplaced in a dark chamber at about 20° C. and 100% relative atmospherichumidity.

Two days after the inoculation, the size of the infected areas on theleaves is evaluated. 0% means an efficacy which corresponds to that ofthe control, whereas an efficacy of 100% means that no infection isobserved.

TABLE C Botrytis test (bean)/protective Application rate Activeingredient according of active Efficacy to the invention compound ing/ha in %

500 84

500 100

500 100

500 87

500 100

500 100

500 100

500 100

500 100

Example D

Puccinia test (wheat)/curative Solvent: 50 parts by weight ofN,N-dimethylacetamide Emulsifier: 1 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for curative activity, young plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours. Theplants are then sprayed with the preparation of active compound at thestated application rates.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of 80% to promote the developmentof rust pustules.

Evaluation is carried out 8 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE D Puccinia test (wheat)/curative Application rate Activeingredient according of active Efficacy to the invention ingredient ing/ha in %

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

Example E

Sphaerotheca test (cucumber)/protective Solvent: 49 parts by weight ofN,N-dimethylformamide Emulsifier: 1 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young cucumber plants are sprayed withthe preparation of active compound at the stated application rates. Oneday after the treatment, the plants are inoculated with a sporesuspension of Sphaerotheca fuliginea. The plants are then placed in agreenhouse at 70% relative atmospheric humidity and a temperature of 23°C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE E Sphaerotheca test (cucumber)/protective Application rate Activeingredient according of active Efficacy to the invention compound ing/ha in %

750 100

750 100

750 100

750 100

1. An isopentylcarboxanilide of formula (I)

in which L represents

R¹ represents hydrogen, C₁-C₈-alkyl, or C₁-C₆-haloalkyl, R² representshydrogen, fluorine, chlorine, methyl, or trifluoromethyl, R³ representshalogen, C₁-C₈-alkyl, or C₁-C₈-haloalkyl, and A represents a radical offormula (A1)

in which R¹⁰ represents hydrogen, hydroxyl, formyl, cyano, chlorine,bromine, iodine, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, orC₃-C₆-cycloalkyl; or represents C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, orC₁-C₄-haloalkylthio having in each case 1 to 5 halogen atoms; orrepresents aminocarbonyl or aminocarbonyl-C₁-C₄-alkyl, R¹¹ representshydrogen, chlorine, bromine, iodine, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy,or C₁-C₄-alkylthio; or represents C₁-C₄-haloalkyl or C₁-C₄-haloalkylthiohaving in each case 1 to 5 halogen atoms, and R¹² represents hydrogen,C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl, or C₁-C₄-alkoxy-C₁-C₄-alkyl; representsC₁-C₄-haloalkyl, C₁-C₄-haloalkylthio-C ₁-C₄-alkyl,C₁-C₄-haloalkoxy-C₁-C₄-alkyl having in each case 1 to 5 halogen atoms;or represents phenyl, with the proviso that R¹⁰ does not representiodine if R¹¹ represents hydrogen.
 2. An isopentylcarboxanilide offormula (I) according to claim 1 in which L represents

R¹ represents hydrogen, C₁-C₆-alkyl, or C₁-C₄-haloalkyl, R² representshydrogen, fluorine, chlorine, methyl, or trifluoromethyl, R³ representsfluorine, chlorine, bromine, iodine, C₁-C₆-alkyl, or C₁-C₆-haloalkylhaving 1 to 13 fluorine, chlorine, and/or bromine atoms, and Arepresents a radical of formula (A1)

in which R¹⁰ represents hydrogen, hydroxyl, formyl, cyano, chlorine,bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio,ethylthio, or cyclopropyl; represents C₁-C₂-haloalkyl orC₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine, and/orbromine atoms; represents trifluoromethylthio, difluorome-thylthio,aminocarbonyl, aminocarbonylmethyl, or amino-carbonylethyl, R¹¹represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxy,ethoxy, methylthio, ethylthio, or C₁-C₂-haloalkyl having 1 to 5fluorine, chlorine. and/or bromine atoms, and R¹² represents hydrogen,methyl, ethyl, n-propyl, isopropyl, C₁-C₂-haloalkyl having 1 to 5fluorine, chlorine, and/or bromine atoms, hydroxymethyl, hydroxyethyl,cyclopropyl, cyclopentyl, cyclohexyl, or phenyl, with the proviso thatR¹⁰ does not represent iodine if R¹¹ represents hydrogen.
 3. Anisopentylcarboxanilide of formula (I) according to claim 1 in which R¹represents hydrogen.
 4. A composition for controlling phytopathogenicfungi comprising one or more isopentylcarboxanilides of formula (I)according to claim 1 and one or more extenders and/or surfactants.
 5. Amethod for controlling phytopathogenic fungi comprising applying aneffective amount of an isopentylcarboxanilide of formula (I) accordingto claim 1 to the microorganisms and/or their habitat.